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Article Navigation >  Green Energy&Environment  > 2020  >  5(4): 484-491
Shengtai Hou, Yunhao Sun, Xueguang Jiang, Pengfei Zhang. Nitrogen-rich isoindoline-based porous polymer: Promoting knoevenagel reaction at room temperature. Green Energy&Environment, 2020, 5(4): 484-491. doi: 10.1016/j.gee.2020.06.021
Citation: Shengtai Hou, Yunhao Sun, Xueguang Jiang, Pengfei Zhang. Nitrogen-rich isoindoline-based porous polymer: Promoting knoevenagel reaction at room temperature. Green Energy&Environment, 2020, 5(4): 484-491. doi: 10.1016/j.gee.2020.06.021
shu

Nitrogen-rich isoindoline-based porous polymer: Promoting knoevenagel reaction at room temperature

doi: 10.1016/j.gee.2020.06.021
  • a.

    School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240 China

  • b.

    Department of Chemistry, University of Tennessee, TN 37996, USA

More Information
  • Corresponding author: E-mail address: chemistryzpf@sjtu.edu.cn (Pengfei Zhang)
  • Received date 09 February 2020, Accepted date 23 June 2020, RevRecd date 28 April 2020, Available online 29 June 2020, Publish date 31 October 2020,
    Abstract
  • Nitrogen-rich porous organic polymers (POPs) with basic features have already shown promising performance in various organic reactions. But the harsh conditions, tedious synthetic methods and the requirement of specific monomers impede their further application. Herein, we introduce isoindoline chemistry into POP community. An isoindoline formation process between aniline and bromomethylbenzene—coupling nucleophilic substitution, HBr elimination, and intramolecular cyclization in one pot, is utilized for POPs synthesis. Nitrogen-rich isoindoline-based porous polymers (IPPs) were obtained with specific surface areas up to 408 m2 g−1. Unexpectedly, mechanochemistry could enable the rapid (3 h) and solid-state synthesis of IPP catalysts. Moreover, this nitrogen-rich catalyst presents excellent activity (isolated yield: 99%), scalable ability (up to 14 g per run) and recyclability (five runs) towards the Knoevenagel condensation reaction under mild reaction conditions (water as solvent at room temperature).

     

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    • References(69)
  • [1]
    E. Merino, E. Verde-Sesto, E.M. Maya, M. Iglesias, F. Sanchez, A. Corma, Chem. Mater. 25 (2013) 981-988
    [2]
    Y. Zhang, S.N. Riduan, Chem. Soc. Rev. 41 (2012) 2083-2094
    [3]
    X. Du, Y. Sun, B. Tan, Q. Teng, X. Yao, C. Su, W. Wang, Chem. Commun. 46 (2010) 970-972
    [4]
    F. Hoffmann, M. Cornelius, J. Morell, M. Froba, Angew. Chem. Int. Ed. 45 (2006) 3216-3251
    [5]
    H. Ma, H. Ren, S. Meng, Z. Yan, H. Zhao, F. Sun, G. Zhu, Chem. Commun. 49 (2013) 9773-9775
    [6]
    H. Oh, S.B. Kalidindi, Y. Um, S. Bureekaew, R. Schmid, R.A. Fischer, M. Hirscher, Angew. Chem. Int. Ed. 52 (2013) 13219-13222
    [7]
    K.E. Maly, J. Mater. Chem. 19 (2009) 1781
    [8]
    R.E. Morris, P.S. Wheatley, Angew. Chem. Int. Ed. 47 (2008) 4966-4981
    [9]
    J.X. Jiang, F. Su, A. Trewin, C.D. Wood, H. Niu, J.T. Jones, Y.Z. Khimyak, A.I. Cooper, J. Am. Chem. Soc. 130 (2008) 7710-7720
    [10]
    F. Svec, J.M.J. Frechet, Macromolecules 28 (1995) 7580-7582
    [11]
    F. Tang, H. Fudouzi, T. Uchikoshi, Y. Sakka, J. Eur. Ceram. Soc. 24 (2004) 341-344
    [12]
    P.M. Budd, B.S. Ghanem, S. Makhseed, N.B. McKeown, K.J. Msayib, C.E. Tattershall, Chem. Commun. (2004) 230-231
    [13]
    N.B. McKeown, P.M. Budd, Chem. Soc. Rev. 35 (2006) 675-683
    [14]
    N.B. McKeown, P.M. Budd, K.J. Msayib, B.S. Ghanem, H.J. Kingston, C.E. Tattershall, S. Makhseed, K.J. Reynolds, D. Fritsch, Chem. 11 (2005) 2610-2620
    [15]
    O.K. Farha, A.M. Spokoyny, B.G. Hauser, Y.-S. Bae, S.E. Brown, R.Q. Snurr, C.A. Mirkin, J.T. Hupp, Chem. Mater. 21 (2009) 3033-3035
    [16]
    R. Dawson, L.A. Stevens, T.C. Drage, C.E. Snape, M.W. Smith, D.J. Adams, A.I. Cooper, J. Am. Chem. Soc. 134 (2012) 10741-10744
    [17]
    M.G. Schwab, A. Lennert, J. Pahnke, G. Jonschker, M. Koch, I. Senkovska, M. Rehahn, S. Kaskel, J. Mater. Chem. 21 (2011) 2131-2135
    [18]
    C.D. Wood, B. Tan, A. Trewin, H. Niu, D. Bradshaw, M.J. Rosseinsky, Y.Z. Khimyak, N.L. Campbell, R. Kirk, E. Stockel, A.I. Cooper, Chem. Mater. 19 (2007) 2034-2048
    [19]
    J.Y. Lee, C.D. Wood, D. Bradshaw, M.J. Rosseinsky, A.I. Cooper, Chem. Commun. (2006) 2670-2672
    [20]
    J. Germain, J. Hradil, J.M.J. Frechet, F. Svec, Chem. Mater. 18 (2006) 4430-4435
    [21]
    T. Ma, E.A. Kapustin, S.X. Yin, L. Liang, Z. Zhou, J. Niu, L.H. Li, Y. Wang, J. Su, J. Li, X. Wang, W.D. Wang, W. Wang, J. Sun, O.M. Yaghi, Science 361 (2018) 48-52
    [22]
    S. Kandambeth, K. Dey, R. Banerjee, J. Am. Chem. Soc. 141 (2018) 1807-1822
    [23]
    C.S. Diercks, O.M. Yaghi, Science 355 (2017) 923-933
    [24]
    A.P. Cote, A.I. Benin, N.W. Ockwig, M. O'Keeffe, A.J. Matzger, O.M. Yaghi, Science 310 (2005) 1166-1170
    [25]
    Z. Xiang, D. Cao, J. Mater. Chem. A 1 (2013) 2691-2718
    [26]
    Y. Zhu, H. Long, W. Zhang, Chem. Mater. 25 (2013) 1630-1635
    [27]
    D. Yuan, W. Lu, D. Zhao, H.C. Zhou, Adv. Mater. 23 (2011) 3723-3725
    [28]
    H. Ren, T. Ben, E. Wang, X. Jing, M. Xue, B. Liu, Y. Cui, S. Qiu, G. Zhu, Chem. Commun. 46 (2010) 291-293
    [29]
    Y. Xu, S. Jin, H. Xu, A. Nagai, D. Jiang, Chem. Soc. Rev. 42 (2013) 8012-8031
    [30]
    P. Kuhn, A. Thomas, M. Antonietti, Macromolecules 42 (2009) 319-326
    [31]
    P. Kuhn, M. Antonietti, A. Thomas, Angew. Chem. Int. Ed. 47 (2008) 3450-3453
    [32]
    T. Ben, C. Pei, D. Zhang, J. Xu, F. Deng, X. Jing, S. Qiu, Energy Environ. Sci. 4 (2011) 3991-3999
    [33]
    L. Zou, D. Feng, T.-F. Liu, Y.-P. Chen, S. Fordham, S. Yuan, J. Tian, H.-C. Zhou, Chem. Commun. 51 (2015) 4005-4008
    [34]
    G. Yang, H. Han, C. Du, Z. Luo, Y. Wang, Polymer 51 (2010) 6193-6202
    [35]
    R.W. Tilford, W.R. Gemmill, H.-C. zur Loye, J.J. Lavigne, Chem. Mater. 18 (2006) 5296-5301
    [36]
    A.G. Nasibulin, P.V. Pikhitsa, H. Jiang, D.P. Brown, A.V. Krasheninnikov, A.S. Anisimov, P. Queipo, A. Moisala, D. Gonzalez, G. Lientschnig, A. Hassanien, S.D. Shandakov, G. Lolli, D.E. Resasco, M. Choi, D. Tomanek, E.I. Kauppinen, Nat. Nanotech. 2 (2007) 156-161
    [37]
    P. Yang, S. Gai, J. Lin, Chem. Soc. Rev. 41 (2012) 3679-3698
    [38]
    H.B. Wu, J.S. Chen, H.H. Hng, X.W. Lou, Nanoscale 4 (2012) 2526-2542
    [39]
    D. Wu, F. Xu, B. Sun, R. Fu, H. He, K. Matyjaszewski, Chem. Rev. 112 (2012) 3959-4015
    [40]
    B.K. Wilk, Tetrahedron 53 (1997) 7097-7100
    [41]
    B. Tamami, A. Fadavi, Catal. Commun. 6 (2005) 747-751
    [42]
    L.G. Voskressensky, A.A. Festa, A.V. Varlamov, Tetrahedron 70 (2014) 551-572
    [43]
    H. Qin, Y. Zhou, Q. Zeng, H. Cheng, L. Chen, B. Zhang, Z. Qi, Green Energy Environ. (2019) 124-129.
    [44]
    Y. Cui, J. Du, Y. Liu, Y. Yu, S. Wang, H. Pang, Z. Liang, J. Yu, Polym. Chem. 9 (2018) 2643-2649
    [45]
    B. List, Angew. Chem. Int. Ed. 49 (2010) 1730-1734
    [46]
    G. Tuci, L. Luconi, A. Rossin, E. Berretti, H. Ba, M. Innocenti, D. Yakhvarov, S. Caporali, C. Pham-Huu, G. Giambastiani, ACS Appl. Mater. Interfaces 8 (2016) 30099-30106
    [47]
    M.M. Kabat, A. Kurek, J. Wicha, J. Org. Chem. 48 (1983) 4248-4251
    [48]
    J.P.H. Li, M. Stockenhuber, Catal. Today 245 (2015) 108-115
    [49]
    B.M. Reddy, M.K. Patil, K.N. Rao, G.K. Reddy, J. Mol. Catal. A Chem. 258 (2006) 302-307
    [50]
    K. Ikeue, N. Miyoshi, T. Tanaka, M. Machida, Catal. Lett. 141 (2011) 877
    [51]
    V. Calvino-Casilda, M. Olejniczak, R. Maria Martin-Aranda, M. Ziolek, Micropor. Mesopor. Mater. 224 (2016) 201-207
    [52]
    R. Wirz, D. Ferri, A. Baiker, Langmuir 22 (2006) 3698-3706
    [53]
    K. Motokura, N. Viswanadham, G.M. Dhar, Y. Iwasawa, Catal. Today 141 (2009) 19-24
    [54]
    T. Seki, M. Onaka, J. Mol. Catal. A Chem. 263 (2007) 115-120
    [55]
    L. Wang, G. Xu, J. Xiao, M. Tao, W. Zhang, Ind. Eng. Chem. Res. 58 (2019) 12401-12410
    [56]
    B. Tamami, A. Fadavi, Iranian Polymer Journal 15 (2006) 331-339
    [57]
    M. Almasi, V. Zelenak, M.V. Opanasenko, J. Cejka, Catal Lett 148 (2018) 2263-2273
    [58]
    L. Song, C. Chen, X. Chen, N. Zhang, Chem. Res. Chin. Univ. 32 (2016) 838-842
    [59]
    X. Wu, B. Wang, Z. Yang, L. Chen, J. Mater. Chem. A 7 (2019) 5650-5655
    [60]
    P. Makowski, J. Weber, A. Thomas, F. Goettmann, Catal. Commun. 10 (2008) 243-247
    [61]
    X.-J. Zhang, N. Bian, L.-J. Mao, Q. Chen, L. Fang, A.-D. Qi, B.-H. Han, Mater. Chem. Phys. 213 (2012) 1575-1581
    [62]
    Y. Wang, L. Wang, C. Liu, R. Wang, ChemCatChem 7 (2015) 1559-1565
    [63]
    E. Kandasamy, S. Nagarajan, T.M. Shaikh, Lett. Org. Chem. 15 (2018) 133-138
    [64]
    P. Gogoi, K. Boruah, R. Borah, Chemistryselect 3 (2018) 9476-9483
    [65]
    F. Santamarta, P. Verdia, E. Tojo, Catal. Commun. 9 (2008) 1779-1781
    [66]
    J. Lu, P.H. Toy, Chem. Rev. 109 (2009) 815-838
    [67]
    Y. Ju, R.S. Varma, J. Org. Chem. 71 (2006) 135-141
    [68]
    P. Thapa, E. Corral, S. Sardar, B.S. Pierce, F.W. Foss, J. Org. Chem. 84 (2018) 1025-1034
    [69]
    R.S. Bitzer, L.C. Visentin, M. Horner, M.A.C. Nascimento, C.A.L. Filgueiras, Journal of Coordination Chemistry 70 (2017) 1089-1104
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